So if Mr. Thiel this week gave himself the job of speaking for a candidate whom many of his Silicon Valley friends and peers frankly revile, one readily supposes the reasoning went like this: The Valley sees Trump as anti-trade, anti-immigration, and nothing in Mr. Thiel’s speech suggested Mr. Thiel is anti-trade, anti-immigration. But Mr. Trump is a wrecking ball at a time when Washington needs a wrecking ball. It needs a candidate whose very existence forcibly disrupts its ways and patterns.

But Jenkins goes sideways, as he always does in my opinion, when he leaves the question open of whether Trump is that “wrecking ball” candidate.

In every other way, Mr. Trump sticks to a diagnosis that blames non-Americans for America’s problems. We wait to find out how this plays with the American voter. Politically, Mr. Trump piles his chips on a high-risk, all-or-nothing gamble. He seeks to ignite a populist prairie fire that will burn a path to the White House. He does not engage in the tactical (and expensive, media-wise) base broadening that most presidential campaigns engage in.

Why do progressives reject Hillary Clinton? The highly educated, high-income, finance-literate readers of my website, Naked Capitalism, don’t just overwhelmingly favor Bernie Sanders. They also say “Hell no!” to Hillary Clinton to the degree that many say they would even vote for Donald Trump over her.

And they don’t come by these views casually. Their conclusions are the result of careful study of her record and her policy proposals. They believe the country can no longer endure the status quo that Clinton represents—one of crushing inequality, and an economy that is literally killing off the less fortunate—and any change will be better.

Trump is not that guy. Trump is cynical in a more conventional way than, for example, Sloterdijk’s Kynic. Trump thinks everyone is an idiot. In the same way Diogenes challenged Socrates by completely disrespecting him, by throwing civility to the dogs and stooping to vulgarity, Trump upended the “respectable” political cognoscenti —GOP establishment and the mainstream media.

Trump plays the fool, like Diogenes, but not on behalf of gleefully liberating us from a political tradition that constrains our reason. Trump uses sarcasm, but he does not use it to liberate the political opposition to critique official culture. Trump hates opposition of any kind. You are either with him or against him. Just look at how he lashed back at Ted Cruz, who refused to endorse him from the stage of the convention.

Trump is a member of official culture and its false idealism (“Make America great again”) and repression (for example, he’s opposed to non-traditional marriage), and too much a part of the traditional bigotry and prejudice against groups that official culture denigrates when he associates them with the body and its functions (women and Mexicans, for example).

Finally, Trump is a rich guy who brags about his success accomplished via old-fashioned capitalism, including avoiding taxes and using the law, especially the bankruptcy code and non-stop litigation, to gain an advantage over business partners, employers and vendors.

Trump’s power is the kind of emptiness Diogenes was trying to expose.

Trump’s supporters are cynical in another colloquial sense, throwing around around negativity as a weapon in an arch, pseudo-ironic way. Do they really mean it when they say, “Trump is great, I love it, it would be the end of the world of he were elected, I’m voting for him”?

Several other writers tried their hand at analyzing the Thiel – Trump connection before the speech.

Greg Ferenstein, author of “The Age of Optimists,” a book about tech and politics, has studied start-up founders’ political views. He has found that while founders tend to support some libertarian points of view (they are for free trade and tend to be skeptical of labor unions), they are generally aligned with Democrats on many major policy areas. They are for increased immigration, for greater environmental protections, for more government spending on research and infrastructure, and for health care mandates like the one in the Affordable Care Act, among other ideas.

People in Silicon Valley “are supporting policies that are very much pro-capitalism and pro-government at the same time,” Mr. Ferenstein wrote last year. He added, “No, Silicon Valley is not a libertarian hotbed; rather, we are witnessing the rise of an entirely new type of Democrat.

The timing, according to an investor who knows him, was classic Thiel: “He’s always thinking, ‘How can I use this to move my agenda forward?’ ” Another acquaintance, a founder of a startup in which Thiel is an investor, says with a mix of fear and admiration, “He’s diabolical.”

“Every time I read [of Thiel’s support for Trump], I typically check the calendar because I’m not completely sure it’s not April 1,” said Max Levchin, Thiel’s friend and PayPal co-founder, at a June conference, after recovering from a giggling fit. He went on: “It wouldn’t surprise me if the underlying reality of his choice were the sheer contrariness of what he is doing.” (Levchin declined to comment further.)

Readers of this blog know that I wrote a paper on Thiel and his politics for my Master’s degree. The three-part series can be found here:

Postscript: In a new film by Rebecca Miller called Maggie’s Plan, Slavoj Žižek, the Slovenian psychoanalytic philosopher, cultural critic, and Hegelian Marxist is referenced although he does not make an appearance. From The New York Times review:

Slavoj Žižek, who has appeared in several movies but (spoiler alert) does not show up in this one. Still, his name is not dropped in vain. In his writing on, for example, Alfred Hitchcock’s films and Jane Austen’s novels, Mr. Žižek has proven to be an acute analyst of the ways that plots reach their destinations through misrecognition and error. People get what they think they want in order to discover what they really want. Control is illusory. Desire is perverse.Outcomes are unpredictable until the moment they are revealed as inevitable.

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Francine McKenna (@retheauditors) is the Transparency Reporter at MarketWatch.com, a Dow Jones publication, where her work is also featured frequently in the Wall Street Journal. McKenna had more than twenty-five years of experience in consulting and professional services including tenure at two Big 4 firms, both in the US and abroad before becoming a journalist. Look for her prior columns, "Accounting Watchdog" at Forbes.com and "Accountable" at American Banker. For more information, click "About" at the bottom of this page. For more information contact Francine McKenna, fmckenna@mckennapartners.com